Both sides' armies during the Anarchy probably ranged from around 5,000 to 7,000 men; the size of Matilda's force at Oxford is unknown but comprised only a small court of a few barons.
The siege of Oxford took place during the Anarchy, a period of civil war following the death of Henry I of England without a male heir, in 1142. Fought between his nephew, Stephen of Blois, and his daughter, the Empress Matilda (or Maud), who had recently been expelled from her base in Westminster and chosen the City of Oxford as her new headquarters. Oxford by now was effectively a regional capital and important in its own right. It was a well-defended city with both rivers and walls protecting it, and was also strategically important as it was at a crossroads between the north, south-east and west of England, and also not far from London.
By now the civil war was at its height, yet neither party was able to get an edge on the other: both had suffered swings of fate in the last few years which had alternately put them ahead, and then behind, their rival. Stephen, for instance, had been captured by Matilda's army in 1141, but later in the year, Matilda's half-brother and chief military commander, Robert, Earl of Gloucester was captured by Stephen's army. Likewise, Matilda had been recognised as "Lady of the English" but had not long afterwards been run out of London.
Stephen believed that all it would take to win the war decisively would be to capture Matilda herself; her escape to Oxford seemed to present him with such an opportunity. Having raised a large army in the north, he returned south and attacked Wareham in Dorset; this port town was important to Matilda's Angevin party as it provided one of the few direct links to the continent that they controlled. He attacked and captured more towns as he returned to the Thames Valley, and soon the only significant base Matilda had outside of the south-west—apart from Oxford itself—was at Wallingford Castle, held by her close supporter Brian Fitz Count.
Stephen's army approached Oxford on 26 September 1142, and according to contemporary accounts, swam his army across the rivers and waterways that blocked the approach to the city. Matilda's small force was taken by surprise. Those that were not killed or captured retreated into the castle; Stephen now controlled the city, which protected him from counterattack. The king knew he was unlikely to be able to take the castle by force—although that did not stop him from using the latest siege technology. He also knew that it would be a long, hard wait before Matilda was starved out. But after nearly three months of siege, conditions for the garrison were dire, and they formed a plan to help the Empress escape from under Stephen's nose. One early December evening Matilda crept out of a postern door in the wall—or, more romantically, possibly shinned down on a rope out of St George's Tower—dressed in white as camouflage against the snow and passed without capture through Stephen's lines. She escaped to Abingdon Abbey and then to Wallingford Castle where she was safe; Oxford Castle surrendered to Stephen the following day, and the war continued punctuated by a series of sieges for the next 11 years.
The site of Siege of Oxford Castle (The Anarchy) lies on Kellaways Formation And Oxford Clay Formation (Undifferentiated), bedrock that formed in the Oxfordian. The rock here is mudstone, siltstone and sandstone.
On a December evening in 1142, with Stephen's forces encircling a castle reduced to desperate straits by nearly three months of siege, the Empress Matilda slipped out through a postern door, or possibly shinned down a rope from St George's Tower, clad in white robes that blended with the snow, and walked without capture through the king's own lines to safety at Abingdon Abbey and then Wallingford Castle; the castle surrendered to Stephen the following morning, yet his great prize had vanished into the winter night.
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